2-(4-Bromophenoxy)-5-nitropyridine → 6-(4-bromophenoxy)pyridin-3-amine

HRID 1760361Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)=[CH:4][CH:3]=1>O=[Pt]=O.CO>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 2-(4-bromo-phenoxy)-5-nitro-pyridine (6.0 g, 22.7 mmol), 200 mL of methanol and 50 mg of PtO2 was shaken under 50 psi of H2 for 1 hour at 23° C. The mixture was filtered through a pad of celite® and the filtrate was concentrated in vacuo, affording 6 g of 6-(4-bromo-phenoxy)-pyridin-3-ylamine. 1H NMR (CD3OD, 500 MHz): 7.65 (d, 1H, J=3.5 Hz), 7.48 (d, 2H, J=8.5 Hz), 7.25 (dd, 1H, J=3.5, 9.0 Hz), 6.91 (d, 2H, J=9.0 Hz), 6.80 (d, 1H, J=9.0 Hz) ppm. MS (APCl, m/z): 265 [M+H]+.

Workup

filtrationThe mixture was filtered through a pad of celite®
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-435fd8a32a834aedb0467ecbf5b4b852
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841671B2

Reaction notes

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